Dunedin: A Taste of Old Florida in Tampa Bay
Have you ever visited Dunedin, Florida? Nestled along the Gulf Coast, Dunedin is one of the oldest towns on the West Coast of Florida, and just west of Tampa Bay. Offering a picturesque lush, woodsy, forest to beach vibe, Dunedin sings old Florida character along four miles of relaxing beachfront. Known for its small-town feel, picturesque views, and rich cultural heritage, Dunedin is a hidden gem that has been gaining popularity among travelers in recent years.
Check out my Dunedin vlog with Visit St. Pete/Clearwater and stay at the Fenway Hotel above!
1. Stroll the Scenic Pinellas Trail
This 47-mile paved path weaves through downtown Dunedin and hugs the coast, offering picturesque views of the Gulf. Perfect for walking, biking, or cafe-hopping your way through town.
2. Dive into Local History
The Dunedin Historical Museum — housed in a restored railroad depot — tells the town’s story, from its citrus roots to its role in Florida’s military past. A must-stop for a bit of local flavor and nostalgia.
3. Explore Honeymoon Island State Park
Just a short drive away, this natural paradise features miles of untouched beach, winding nature trails, and plenty of opportunities for kayaking, swimming, or simply soaking up the sun.
4. Celebrate the Culture
Dunedin knows how to throw a party! Time your visit with one of the town’s signature festivals — think Dunedin Celtic Festival or Mardi Gras — for a full dose of live music, food, and lively community spirit.
5. Indulge in the Local Food Scene
From fresh seafood to Scottish favorites, Dunedin’s culinary offerings are a delicious surprise. You’ll find everything from cozy cafes to elevated dining experiences, and it’s all served with small-town warmth.
Where to Stay: The Fenway Hotel – A Piece of Florida History
Once a Jazz Age icon, The Fenway Hotel has been reimagined as a modern-day retreat that stays true to its musical roots. With sweeping views of the bay, a rooftop pool, and bold art deco design, it’s both a feast for the eyes and the soul.
Don’t miss the rooftop experience at Hi-Fi Rooftop Bar, where sunset views of Caladesi and Honeymoon Islands are paired with creative cocktails, local brews, and a soundtrack of live jazz or DJ beats. Fun fact: this is the very spot where radio history began in 1925, when a 500-watt transmitter was installed on the roof to broadcast Florida’s first AM directional signal.
Historic elegance meets coastal cool.
The hotel’s jazz-age soul carries through every detail, from curated design touches to lively programming. Even the original speakeasy makes a cameo — with remnants of its entrance still visible in the lobby today.
Dinner at Hew Chophouse
Nestled poolside, this intimate chophouse serves up dry-aged steaks, a seasonal sushi menu, and seafood done right. We shared the tomahawk steak, savored charred octopus, and enjoyed impeccable service that made dinner feel like a celebration.
Dunedin may be small, but it packs a big punch when it comes to things to see and do. Whether you're looking for adventure, relaxation, or a bit of both, Dunedin is the perfect destination for a Florida getaway.
The charming downtown offers history, culture, and a booming food and beverage scene with top-tier restaurants that will bring you back to the coastal town for more flavors. A few of those shining stars are the Hi-Fi Rooftop and Hew Chophouse. Both set in the historic Fenway Hotel, you’ll want to plan a stay just to eat, play, and lounge by the pool — all perfectly positioned in the heart of Downtown Dunedin for easy exploration.
There’s a portion of the original speakeasy at the Fenway Hotel which sits at the lobby now and visible to visitors. It’s so cool because you can actually see a preserved portion of the speakeasy entrance that was once located in the basement (as a speakeasy should be). The hotel’s current day watering hole now sits high above prohibition laws, at the scenic rooftop — the HiFi Rooftop.
Not only does the the rooftop bar offer pristine sunset views of Caladesi and Honeymoon Islands, with a side of delicious cocktails, local craft beers, wines, and tasty bites to enjoy — the story of radio and AM directional antennas began in 1925 with George W. Bowles at the same rooftop of the Fenway Hotel —
My parents both worked in radio so I found this tidbit so intriguing, that guests get to quite literally live and enjoy a bit of radio history. I also love how the entire Fenway Hotel is designed around the historic jazz age era, from the amenities to bold decor and lively ambience.
After waterfront drinks and apps at Hi-Fi, make your way down to Hew Chophouse for dinner and live music. Enjoy aged steaks, chophouse classics, and a seasonal sushi menu with a fantastic wine and cocktail selection. This intimate spot overlooks the pool, perfect for an al fresco lunch or a celebratory dinner.
We enjoyed delicious seafood, the charred octopus, and split a tomahawk steak which while incredibly large, still tender and delicious. The service was as impeccable as the cuisine and made for the perfect prelude to a fabulous evening roaming the property.
The Fenway actually pays homage to Florida’s colorful past with a daily sunset celebration. Those dreamy Dunedin views via the hotel lawn were my favorite backdrop for a glass of wine under the moonlight.
Don’t Miss:
– Sunset lawn celebrations with wine in hand
– Morning Tai Chi or yoga on the historic lawn
– Exploring downtown Dunedin by complimentary bike
– Local hot spots like Dunedin Brewery, Sonder Social Club, and The Restorative
During the day you can soak up the rays at the pool or take in the gorgeous local sights via bicycles ride, complimentary to guests. Visitors can roam the manicured grounds, relax on the veranda or take in the waterfront views from the rooftop of the expansive bay. Partake in activities on the historic lawn, including Tai Chi classes and yoga. We made our way off-property to visit the very picturesque and walkable Main Street, which includes an array of unique restaurants and watering holes, which will knock your socks off. Some of my favorites include the Dunedin Brewery, Sonder Social Club, and The Restorative Restaurant.
Dunedin is everything you didn’t know you needed. Think relaxing coastal charm with big personality and even bigger flavor. For the ultimate stay, book a weekend at The Fenway Hotel and let this Florida gem sweep you off your feet.
